# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Tomislav Friscic' _publ_contact_author_address ; Lensfield Road Cambridge CB2 1EW ; _publ_contact_author_email WJ10@CAM.AC.UK loop_ _publ_author_name D.Cincic T.Friscic W.Jones # Attachment '- deposit_revised.cif' data_(1,4-tfib)2-(dithiane) _database_code_depnum_ccdc_archive 'CCDC 795734' #TrackingRef '- deposit_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-DIIODOTETRAFLUOROBENZENE - 1,4-DITHIANE 2/1 ; _chemical_name_common '1,4-DIIODOTETRAFLUOROBENZENE - 1,4-DITHIANE 2/1' _chemical_melting_point ? _chemical_formula_moiety '2(C6 F4 I2), (C4 H8 S2)' _chemical_formula_sum 'C16 H8 F8 I4 S2' _chemical_formula_weight 923.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3597(2) _cell_length_b 8.6865(2) _cell_length_c 11.2216(3) _cell_angle_alpha 69.182(1) _cell_angle_beta 89.501(1) _cell_angle_gamma 81.866(1) _cell_volume 573.04(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5598 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 5.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.420 _exptl_absorpt_correction_T_max 0.581 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9657 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 32.03 _reflns_number_total 3969 _reflns_number_gt 3136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.8341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3969 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.26332(4) 0.46036(3) 0.34781(3) 0.03503(9) Uani 1 1 d . . . I2 I 0.26952(4) 0.93258(3) -0.17167(3) 0.03423(9) Uani 1 1 d . . . S1 S 0.50760(18) 0.15565(14) 0.56325(10) 0.0347(2) Uani 1 1 d . . . F1 F -0.3424(4) 0.5694(4) 0.0457(3) 0.0418(6) Uani 1 1 d . . . F2 F -0.1393(5) 0.7491(4) -0.1524(2) 0.0423(6) Uani 1 1 d . . . F3 F 0.3438(5) 0.8276(4) 0.1309(3) 0.0520(8) Uani 1 1 d . . . F4 F 0.1420(5) 0.6455(5) 0.3284(3) 0.0542(8) Uani 1 1 d . . . C1 C 0.0722(7) 0.6684(5) 0.2100(4) 0.0341(8) Uani 1 1 d . . . C2 C -0.1043(6) 0.6005(5) 0.1932(4) 0.0280(7) Uani 1 1 d . . . C3 C -0.1730(6) 0.6312(5) 0.0685(4) 0.0278(7) Uani 1 1 d . . . C4 C -0.0678(6) 0.7267(5) -0.0339(4) 0.0297(7) Uani 1 1 d . . . C5 C 0.1091(6) 0.7941(5) -0.0172(4) 0.0279(7) Uani 1 1 d . . . C6 C 0.1771(7) 0.7624(5) 0.1083(4) 0.0337(8) Uani 1 1 d . . . C7 C 0.3297(6) 0.1615(5) 0.4361(4) 0.0366(9) Uani 1 1 d . . . H7A H 0.2006 0.2369 0.4338 0.044 Uiso 1 1 calc R . . H7B H 0.3964 0.2057 0.3554 0.044 Uiso 1 1 calc R . . C8 C 0.7287(6) 0.0077(5) 0.5497(4) 0.0348(8) Uani 1 1 d . . . H8A H 0.7891 0.0541 0.4671 0.042 Uiso 1 1 calc R . . H8B H 0.8375 -0.0075 0.6146 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03803(15) 0.03482(14) 0.02849(14) -0.00529(11) 0.01044(10) -0.00991(11) I2 0.03632(15) 0.03494(14) 0.02965(14) -0.00738(11) 0.01122(10) -0.01126(11) S1 0.0409(5) 0.0368(5) 0.0280(4) -0.0104(4) 0.0105(4) -0.0140(4) F1 0.0385(13) 0.0518(16) 0.0402(14) -0.0162(12) 0.0025(11) -0.0237(12) F2 0.0468(14) 0.0585(17) 0.0220(11) -0.0110(11) -0.0029(10) -0.0186(13) F3 0.0491(16) 0.075(2) 0.0388(15) -0.0181(15) 0.0033(13) -0.0389(16) F4 0.0578(18) 0.085(2) 0.0231(12) -0.0141(14) -0.0027(12) -0.0328(17) C1 0.038(2) 0.042(2) 0.0210(17) -0.0075(16) 0.0023(15) -0.0142(17) C2 0.0282(16) 0.0292(16) 0.0258(17) -0.0076(14) 0.0044(13) -0.0077(13) C3 0.0296(17) 0.0271(16) 0.0275(17) -0.0084(14) 0.0022(14) -0.0102(14) C4 0.0327(18) 0.0349(18) 0.0215(16) -0.0080(14) 0.0033(14) -0.0106(15) C5 0.0288(16) 0.0274(16) 0.0258(17) -0.0063(14) 0.0056(13) -0.0069(13) C6 0.0339(19) 0.041(2) 0.0287(19) -0.0123(17) 0.0042(15) -0.0147(16) C7 0.0270(17) 0.036(2) 0.038(2) -0.0032(17) -0.0001(16) -0.0036(15) C8 0.0252(16) 0.044(2) 0.0298(19) -0.0050(17) -0.0003(14) -0.0103(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C2 2.081(4) . ? I2 C5 2.081(4) . ? S1 C8 1.810(5) . ? S1 C7 1.810(5) . ? F1 C3 1.334(4) . ? F2 C4 1.347(4) . ? F3 C6 1.336(5) . ? F4 C1 1.341(4) . ? C1 C6 1.375(5) . ? C1 C2 1.383(5) . ? C2 C3 1.390(5) . ? C3 C4 1.387(5) . ? C4 C5 1.383(5) . ? C5 C6 1.395(5) . ? C7 C8 1.520(6) 2_656 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C7 1.520(6) 2_656 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S1 C7 100.4(2) . . ? F4 C1 C6 118.5(4) . . ? F4 C1 C2 119.6(4) . . ? C6 C1 C2 121.9(4) . . ? C1 C2 C3 117.3(3) . . ? C1 C2 I1 121.5(3) . . ? C3 C2 I1 121.2(3) . . ? F1 C3 C4 118.9(3) . . ? F1 C3 C2 120.3(3) . . ? C4 C3 C2 120.8(3) . . ? F2 C4 C5 120.0(3) . . ? F2 C4 C3 118.0(3) . . ? C5 C4 C3 122.0(3) . . ? C4 C5 C6 116.9(3) . . ? C4 C5 I2 121.6(3) . . ? C6 C5 I2 121.6(3) . . ? F3 C6 C1 119.0(4) . . ? F3 C6 C5 119.7(4) . . ? C1 C6 C5 121.2(4) . . ? C8 C7 S1 113.6(3) 2_656 . ? C8 C7 H7A 108.8 2_656 . ? S1 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 2_656 . ? S1 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 S1 114.2(3) 2_656 . ? C7 C8 H8A 108.7 2_656 . ? S1 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 2_656 . ? S1 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.900 _refine_diff_density_min -2.567 _refine_diff_density_rms 0.412 data_(1,2-tfib)4-(acr)7 _database_code_depnum_ccdc_archive 'CCDC 795735' #TrackingRef '- deposit_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; acridine:tetrafluoro-1,2-diiodobenzene 7/4 ; _chemical_name_common 'acridine:tetrafluoro-1,2-diiodobenzene 7/4' _chemical_melting_point ? _chemical_formula_moiety '7(C13 H9 N1) 4(C6 F4 I2)' _chemical_formula_sum 'C115 H63 F16 I8 N7' _chemical_formula_weight 2861.8 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3792(1) _cell_length_b 13.2620(2) _cell_length_c 20.9590(4) _cell_angle_alpha 74.809(1) _cell_angle_beta 88.358(1) _cell_angle_gamma 78.396(1) _cell_volume 2463.71(7) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 37969 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1370 _exptl_absorpt_coefficient_mu 2.604 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_T_max 0.843 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 32095 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 30.01 _reflns_number_total 14277 _reflns_number_gt 9752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The asymmetric unit has two 1,4-tfib molecules in general positions and 3.5 acr molcules (with one acr molecule lying about an inversion centre with concomitant C-H and N atom disorder) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+2.2201P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14277 _refine_ls_number_parameters 667 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.10946(3) 0.27678(2) 0.444721(13) 0.03086(7) Uani 1 1 d . . . I2 I 0.18562(3) 0.28792(2) 0.267610(13) 0.02827(7) Uani 1 1 d . . . I3 I 0.01734(3) 0.22523(2) -0.179989(13) 0.03066(7) Uani 1 1 d . . . I4 I 0.07012(3) 0.27489(2) -0.363298(13) 0.03010(7) Uani 1 1 d . . . F5 F -0.3618(3) 0.57553(19) 0.34869(13) 0.0404(6) Uani 1 1 d . . . F6 F -0.0590(3) 0.4704(2) 0.18638(11) 0.0413(6) Uani 1 1 d . . . F7 F -0.1878(3) 0.4562(2) -0.42896(12) 0.0432(6) Uani 1 1 d . . . F8 F -0.4225(3) 0.5654(2) -0.38239(14) 0.0488(7) Uani 1 1 d . . . F9 F -0.4636(3) 0.5273(2) -0.25047(15) 0.0480(7) Uani 1 1 d . . . F10 F -0.1816(3) 0.4411(2) 0.44405(12) 0.0406(6) Uani 1 1 d . . . F11 F -0.2690(3) 0.3834(2) -0.16496(13) 0.0420(6) Uani 1 1 d . . . F12 F -0.2995(3) 0.5928(2) 0.21959(13) 0.0428(6) Uani 1 1 d . . . C95 C 0.4977(18) 0.5072(13) 0.0677(9) 0.026(4) Uani 0.50 1 d PU . . H95 H 0.4929 0.5121 0.1122 0.031 Uiso 0.50 1 calc PR . . N4 N 0.4813(15) 0.4992(11) 0.0663(7) 0.027(4) Uani 0.50 1 d PU . . C94 C 0.3385(5) 0.0305(3) 0.7524(2) 0.0306(9) Uani 1 1 d . . . H94 H 0.2555 0.0869 0.7459 0.037 Uiso 1 1 calc R . . N3 N 0.5844(4) -0.1361(3) 0.77064(16) 0.0273(7) Uani 1 1 d . . . N2 N 0.2214(4) 0.0532(3) 0.91474(17) 0.0288(8) Uani 1 1 d . . . N1 N 0.3070(4) 0.1386(3) 0.56599(18) 0.0325(8) Uani 1 1 d . . . C18 C 0.2641(5) 0.4363(4) 0.0739(2) 0.0383(11) Uani 1 1 d . . . H18 H 0.2553 0.4374 0.1190 0.046 Uiso 1 1 calc R . . C19 C 0.3857(4) 0.4692(3) 0.0378(2) 0.0286(9) Uani 1 1 d . . . C20 C 0.6039(4) 0.5337(3) 0.0297(2) 0.0260(8) Uani 1 1 d . . . C21 C 0.4591(5) -0.1217(3) 0.9375(2) 0.0320(9) Uani 1 1 d . . . H21 H 0.5386 -0.1807 0.9434 0.038 Uiso 1 1 calc R . . C22 C 0.5802(5) 0.3033(4) 0.5307(2) 0.0433(12) Uani 1 1 d . . . H22 H 0.5841 0.3769 0.5190 0.052 Uiso 1 1 calc R . . C23 C 0.3207(4) -0.0750(3) 0.7721(2) 0.0270(9) Uani 1 1 d . . . C24 C 0.7405(5) -0.0095(3) 0.7424(2) 0.0335(10) Uani 1 1 d . . . H24 H 0.8235 -0.0660 0.7497 0.040 Uiso 1 1 calc R . . C25 C 0.2759(7) -0.1808(4) 0.6265(3) 0.0573(15) Uani 1 1 d . . . H25 H 0.2655 -0.2530 0.6410 0.069 Uiso 1 1 calc R . . C26 C 0.3180(4) -0.1392(3) 0.9469(2) 0.0292(9) Uani 1 1 d . . . C27 C 0.3595(5) 0.0679(3) 0.9099(2) 0.0293(9) Uani 1 1 d . . . C28 C 0.0559(5) -0.0659(4) 0.9427(2) 0.0375(11) Uani 1 1 d . . . H28 H -0.0237 -0.0069 0.9318 0.045 Uiso 1 1 calc R . . C29 C 0.2988(5) -0.2894(4) 0.8127(2) 0.0405(11) Uani 1 1 d . . . H29 H 0.2898 -0.3620 0.8264 0.049 Uiso 1 1 calc R . . C30 C -0.0858(5) 0.4592(3) 0.2513(2) 0.0288(9) Uani 1 1 d . . . C31 C 0.7145(5) 0.5694(3) 0.0584(2) 0.0367(10) Uani 1 1 d . . . H31 H 0.7088 0.5715 0.1034 0.044 Uiso 1 1 calc R . . C32 C 0.2007(4) -0.0484(3) 0.9340(2) 0.0269(9) Uani 1 1 d . . . C33 C 0.7080(5) 0.1213(4) 0.5572(2) 0.0441(12) Uani 1 1 d . . . H33 H 0.7966 0.0700 0.5631 0.053 Uiso 1 1 calc R . . C34 C 0.4848(4) -0.0181(3) 0.9195(2) 0.0294(9) Uani 1 1 d . . . C35 C 0.4491(5) 0.2738(4) 0.5393(2) 0.0391(11) Uani 1 1 d . . . H35 H 0.3625 0.3270 0.5329 0.047 Uiso 1 1 calc R . . C36 C -0.2099(4) 0.5237(3) 0.2670(2) 0.0301(9) Uani 1 1 d . . . C37 C 0.3850(5) 0.1741(4) 0.8939(2) 0.0370(10) Uani 1 1 d . . . H37 H 0.3044 0.2324 0.8874 0.044 Uiso 1 1 calc R . . C38 C 0.7108(6) 0.2262(5) 0.5390(2) 0.0502(14) Uani 1 1 d . . . H38 H 0.8014 0.2484 0.5317 0.060 Uiso 1 1 calc R . . C39 C 0.5721(5) 0.0868(4) 0.5675(2) 0.0334(10) Uani 1 1 d . . . C40 C 0.4339(5) -0.2658(3) 0.8020(2) 0.0334(10) Uani 1 1 d . . . H40 H 0.5175 -0.3217 0.8086 0.040 Uiso 1 1 calc R . . C41 C 0.2857(5) -0.2432(3) 0.9694(2) 0.0388(11) Uani 1 1 d . . . H41 H 0.3628 -0.3040 0.9774 0.047 Uiso 1 1 calc R . . C42 C -0.0237(4) 0.3797(3) 0.36594(19) 0.0247(8) Uani 1 1 d . . . C43 C 0.6364(6) 0.1790(4) 0.7122(2) 0.0419(12) Uani 1 1 d . . . H43 H 0.6507 0.2503 0.6982 0.050 Uiso 1 1 calc R . . C44 C 0.0299(5) -0.1667(4) 0.9665(3) 0.0459(12) Uani 1 1 d . . . H44 H -0.0672 -0.1768 0.9745 0.055 Uiso 1 1 calc R . . C45 C 0.1817(5) -0.1043(4) 0.7838(2) 0.0378(11) Uani 1 1 d . . . H45 H 0.0958 -0.0504 0.7773 0.045 Uiso 1 1 calc R . . C46 C -0.1481(4) 0.4445(3) 0.3809(2) 0.0288(9) Uani 1 1 d . . . C47 C 0.3001(5) 0.0339(3) 0.5847(2) 0.0309(9) Uani 1 1 d . . . C48 C -0.3452(5) 0.4729(3) -0.2732(2) 0.0341(10) Uani 1 1 d . . . C49 C 0.6444(5) 0.1089(4) 0.8960(2) 0.0429(12) Uani 1 1 d . . . H49 H 0.7396 0.1238 0.8906 0.052 Uiso 1 1 calc R . . C50 C 0.5612(5) -0.0206(4) 0.5873(2) 0.0396(11) Uani 1 1 d . . . H50 H 0.6471 -0.0745 0.5947 0.047 Uiso 1 1 calc R . . C51 C 0.4500(4) -0.1572(3) 0.78090(19) 0.0271(9) Uani 1 1 d . . . C52 C 0.1616(5) 0.4037(4) 0.0451(3) 0.0443(12) Uani 1 1 d . . . H52 H 0.0811 0.3829 0.0699 0.053 Uiso 1 1 calc R . . C53 C -0.3248(5) 0.4925(3) -0.3401(2) 0.0337(10) Uani 1 1 d . . . C54 C 0.5009(5) 0.1603(3) 0.7221(2) 0.0358(10) Uani 1 1 d . . . H54 H 0.4205 0.2187 0.7157 0.043 Uiso 1 1 calc R . . C55 C 0.1608(5) 0.0051(4) 0.5938(2) 0.0420(11) Uani 1 1 d . . . H55 H 0.0751 0.0592 0.5856 0.050 Uiso 1 1 calc R . . C56 C 0.4761(5) 0.0539(3) 0.7421(2) 0.0298(9) Uani 1 1 d . . . C57 C 0.4394(5) 0.1643(3) 0.5577(2) 0.0306(9) Uani 1 1 d . . . C58 C -0.2040(5) 0.4356(3) -0.3627(2) 0.0290(9) Uani 1 1 d . . . C59 C 0.4111(6) -0.1578(4) 0.6179(2) 0.0477(13) Uani 1 1 d . . . H59 H 0.4948 -0.2137 0.6263 0.057 Uiso 1 1 calc R . . C60 C -0.2448(5) 0.3988(3) -0.2302(2) 0.0299(9) Uani 1 1 d . . . C61 C 0.1472(5) -0.2566(4) 0.9795(2) 0.0443(12) Uani 1 1 d . . . H61 H 0.1279 -0.3264 0.9954 0.053 Uiso 1 1 calc R . . C62 C 0.6251(5) 0.0060(4) 0.9116(2) 0.0410(11) Uani 1 1 d . . . H62 H 0.7078 -0.0505 0.9173 0.049 Uiso 1 1 calc R . . C63 C -0.1231(4) 0.3411(3) -0.2524(2) 0.0244(8) Uani 1 1 d . . . C64 C 0.8274(5) 0.6001(4) 0.0219(3) 0.0450(12) Uani 1 1 d . . . H64 H 0.8998 0.6243 0.0413 0.054 Uiso 1 1 calc R . . C65 C -0.2412(4) 0.5141(3) 0.3325(2) 0.0287(9) Uani 1 1 d . . . C66 C 0.5214(5) 0.1933(4) 0.8879(2) 0.0428(12) Uani 1 1 d . . . H66 H 0.5351 0.2647 0.8780 0.051 Uiso 1 1 calc R . . C67 C 0.0074(4) 0.3870(3) 0.2990(2) 0.0252(8) Uani 1 1 d . . . C68 C 0.7577(5) 0.0934(4) 0.7225(2) 0.0382(11) Uani 1 1 d . . . H68 H 0.8529 0.1080 0.7154 0.046 Uiso 1 1 calc R . . C69 C -0.1014(4) 0.3591(3) -0.3201(2) 0.0257(8) Uani 1 1 d . . . C70 C 0.1499(6) -0.0980(4) 0.6139(3) 0.0515(14) Uani 1 1 d . . . H70 H 0.0563 -0.1157 0.6198 0.062 Uiso 1 1 calc R . . C71 C 0.1715(5) -0.2081(4) 0.8038(2) 0.0415(11) Uani 1 1 d . . . H71 H 0.0788 -0.2267 0.8120 0.050 Uiso 1 1 calc R . . C72 C 0.5990(4) -0.0330(3) 0.7523(2) 0.0295(9) Uani 1 1 d . . . C73 C 0.4266(5) -0.0490(3) 0.5963(2) 0.0348(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03031(15) 0.03229(15) 0.02658(15) -0.00412(11) -0.00193(11) -0.00284(11) I2 0.02531(14) 0.02947(14) 0.02924(15) -0.00847(11) 0.00229(11) -0.00288(11) I3 0.02702(14) 0.03389(15) 0.02974(15) -0.00749(11) -0.00053(11) -0.00396(11) I4 0.02749(14) 0.03185(15) 0.03117(15) -0.00997(11) 0.00426(11) -0.00465(11) F5 0.0286(13) 0.0345(14) 0.0547(17) -0.0139(12) 0.0071(12) 0.0037(11) F6 0.0438(16) 0.0487(16) 0.0238(13) -0.0060(11) -0.0031(12) 0.0042(13) F7 0.0493(17) 0.0409(15) 0.0337(15) -0.0031(12) -0.0025(13) -0.0042(13) F8 0.0374(16) 0.0378(15) 0.0604(19) -0.0014(13) -0.0121(14) 0.0039(12) F9 0.0309(14) 0.0432(16) 0.071(2) -0.0269(14) 0.0093(14) 0.0042(12) F10 0.0427(16) 0.0446(15) 0.0317(15) -0.0119(11) 0.0108(12) -0.0013(12) F11 0.0409(15) 0.0467(16) 0.0403(16) -0.0194(12) 0.0119(12) -0.0039(12) F12 0.0364(15) 0.0404(15) 0.0409(16) -0.0006(12) -0.0102(12) 0.0055(12) C95 0.026(4) 0.026(4) 0.026(4) -0.0068(15) 0.0003(10) -0.0053(13) N4 0.026(4) 0.027(4) 0.026(4) -0.0067(13) 0.0011(10) -0.0052(12) C94 0.028(2) 0.028(2) 0.031(2) -0.0065(17) -0.0053(18) 0.0035(17) N3 0.0261(18) 0.0245(17) 0.0289(19) -0.0062(14) 0.0007(15) -0.0006(14) N2 0.0272(19) 0.0285(18) 0.0288(19) -0.0051(14) -0.0030(15) -0.0040(15) N1 0.0282(19) 0.031(2) 0.038(2) -0.0105(16) 0.0014(16) -0.0036(15) C18 0.040(3) 0.040(3) 0.029(2) -0.0033(19) 0.004(2) 0.000(2) C19 0.026(2) 0.024(2) 0.031(2) -0.0037(17) 0.0016(18) 0.0026(16) C20 0.030(2) 0.0195(19) 0.026(2) -0.0032(15) -0.0013(17) -0.0009(16) C21 0.026(2) 0.033(2) 0.032(2) -0.0069(18) -0.0014(18) 0.0038(18) C22 0.044(3) 0.044(3) 0.040(3) 0.001(2) -0.008(2) -0.019(2) C23 0.025(2) 0.030(2) 0.025(2) -0.0077(16) -0.0029(17) -0.0004(17) C24 0.029(2) 0.034(2) 0.038(3) -0.0107(19) -0.0013(19) -0.0031(19) C25 0.091(5) 0.033(3) 0.050(3) -0.009(2) -0.015(3) -0.016(3) C26 0.028(2) 0.027(2) 0.028(2) -0.0044(17) -0.0041(17) 0.0021(17) C27 0.029(2) 0.034(2) 0.022(2) -0.0038(17) -0.0023(17) -0.0044(18) C28 0.026(2) 0.035(2) 0.048(3) -0.008(2) 0.000(2) -0.0019(19) C29 0.044(3) 0.029(2) 0.049(3) -0.005(2) -0.001(2) -0.014(2) C30 0.030(2) 0.029(2) 0.025(2) -0.0044(17) 0.0001(18) -0.0056(18) C31 0.039(3) 0.034(2) 0.037(3) -0.0109(19) -0.004(2) -0.005(2) C32 0.021(2) 0.031(2) 0.026(2) -0.0055(16) 0.0004(16) -0.0016(16) C33 0.024(2) 0.066(4) 0.036(3) -0.009(2) -0.001(2) 0.000(2) C34 0.026(2) 0.037(2) 0.023(2) -0.0064(17) -0.0022(17) -0.0040(18) C35 0.036(3) 0.036(3) 0.040(3) -0.002(2) -0.005(2) -0.005(2) C36 0.025(2) 0.028(2) 0.035(2) -0.0059(17) -0.0081(18) -0.0013(17) C37 0.030(2) 0.039(3) 0.039(3) -0.007(2) -0.006(2) -0.006(2) C38 0.031(3) 0.079(4) 0.040(3) -0.006(3) 0.001(2) -0.023(3) C39 0.029(2) 0.044(3) 0.027(2) -0.0128(19) 0.0026(18) -0.0031(19) C40 0.034(2) 0.029(2) 0.035(2) -0.0074(18) -0.0004(19) -0.0039(19) C41 0.037(3) 0.025(2) 0.047(3) -0.0037(19) -0.003(2) 0.0016(19) C42 0.022(2) 0.024(2) 0.027(2) -0.0066(16) -0.0007(16) -0.0035(16) C43 0.057(3) 0.028(2) 0.045(3) -0.010(2) -0.001(2) -0.019(2) C44 0.028(3) 0.045(3) 0.062(3) -0.007(2) 0.003(2) -0.010(2) C45 0.020(2) 0.048(3) 0.044(3) -0.012(2) -0.0032(19) -0.0010(19) C46 0.028(2) 0.031(2) 0.030(2) -0.0103(17) 0.0056(18) -0.0081(18) C47 0.032(2) 0.031(2) 0.028(2) -0.0068(17) -0.0060(18) -0.0030(18) C48 0.025(2) 0.027(2) 0.051(3) -0.015(2) 0.003(2) 0.0005(17) C49 0.026(2) 0.062(3) 0.041(3) -0.006(2) 0.003(2) -0.019(2) C50 0.041(3) 0.041(3) 0.030(2) -0.014(2) -0.010(2) 0.015(2) C51 0.029(2) 0.027(2) 0.024(2) -0.0068(16) 0.0017(17) -0.0041(17) C52 0.033(3) 0.041(3) 0.057(3) -0.010(2) 0.006(2) -0.010(2) C53 0.026(2) 0.021(2) 0.052(3) -0.0063(19) -0.008(2) -0.0029(17) C54 0.041(3) 0.023(2) 0.041(3) -0.0082(18) -0.004(2) -0.0017(19) C55 0.038(3) 0.039(3) 0.051(3) -0.013(2) -0.006(2) -0.012(2) C56 0.033(2) 0.027(2) 0.030(2) -0.0102(17) 0.0001(18) -0.0027(18) C57 0.029(2) 0.035(2) 0.026(2) -0.0060(17) -0.0036(18) -0.0037(18) C58 0.031(2) 0.024(2) 0.031(2) -0.0047(17) 0.0001(18) -0.0075(17) C59 0.069(4) 0.032(3) 0.041(3) -0.012(2) -0.011(3) -0.003(2) C60 0.030(2) 0.031(2) 0.033(2) -0.0146(18) 0.0056(18) -0.0097(18) C61 0.043(3) 0.031(2) 0.055(3) -0.001(2) -0.002(2) -0.011(2) C62 0.027(2) 0.052(3) 0.040(3) -0.008(2) 0.000(2) -0.004(2) C63 0.022(2) 0.0199(19) 0.031(2) -0.0093(16) -0.0026(16) -0.0004(15) C64 0.037(3) 0.048(3) 0.055(3) -0.016(2) -0.004(2) -0.016(2) C65 0.023(2) 0.024(2) 0.040(3) -0.0113(18) 0.0026(18) -0.0020(16) C66 0.039(3) 0.045(3) 0.043(3) -0.003(2) -0.007(2) -0.016(2) C67 0.0203(19) 0.024(2) 0.031(2) -0.0090(16) 0.0003(16) -0.0018(15) C68 0.040(3) 0.040(3) 0.039(3) -0.011(2) 0.004(2) -0.018(2) C69 0.022(2) 0.022(2) 0.033(2) -0.0079(16) 0.0027(17) -0.0032(16) C70 0.060(4) 0.051(3) 0.055(3) -0.020(3) -0.002(3) -0.029(3) C71 0.035(3) 0.050(3) 0.039(3) -0.007(2) 0.000(2) -0.016(2) C72 0.027(2) 0.034(2) 0.030(2) -0.0098(18) 0.0029(18) -0.0098(18) C73 0.040(3) 0.033(2) 0.033(2) -0.0120(19) -0.005(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C42 2.098(4) . ? I2 C67 2.112(4) . ? I3 C63 2.116(4) . ? I4 C69 2.092(4) . ? F5 C65 1.346(4) . ? F6 C30 1.352(4) . ? F7 C58 1.353(5) . ? F8 C53 1.341(5) . ? F9 C48 1.345(5) . ? F10 C46 1.344(5) . ? F11 C60 1.347(5) . ? F12 C36 1.340(5) . ? C95 C19 1.471(17) . ? C95 C20 1.303(18) . ? N4 C19 1.271(13) . ? N4 C20 1.448(15) . ? C94 C56 1.384(6) . ? C94 C23 1.394(6) . ? N3 C51 1.345(5) . ? N3 C72 1.354(5) . ? N2 C27 1.345(5) . ? N2 C32 1.353(5) . ? N1 C57 1.347(5) . ? N1 C47 1.355(5) . ? C18 C52 1.346(6) . ? C18 C19 1.428(6) . ? C19 C20 1.426(6) 2_665 ? C20 C19 1.426(6) 2_665 ? C20 C31 1.430(6) . ? C21 C26 1.389(6) . ? C21 C34 1.395(6) . ? C22 C35 1.357(6) . ? C22 C38 1.411(7) . ? C23 C45 1.430(6) . ? C23 C51 1.439(5) . ? C24 C68 1.360(6) . ? C24 C72 1.421(6) . ? C25 C59 1.359(7) . ? C25 C70 1.420(8) . ? C26 C41 1.428(6) . ? C26 C32 1.430(5) . ? C27 C37 1.428(6) . ? C27 C34 1.441(6) . ? C28 C44 1.368(6) . ? C28 C32 1.422(6) . ? C29 C40 1.364(6) . ? C29 C71 1.418(7) . ? C30 C67 1.377(5) . ? C30 C36 1.385(6) . ? C31 C64 1.355(6) . ? C33 C38 1.349(7) . ? C33 C39 1.431(6) . ? C34 C62 1.410(6) . ? C35 C57 1.422(6) . ? C36 C65 1.374(6) . ? C37 C66 1.350(6) . ? C39 C50 1.399(6) . ? C39 C57 1.428(6) . ? C40 C51 1.429(5) . ? C41 C61 1.349(6) . ? C42 C46 1.384(5) . ? C42 C67 1.406(5) . ? C43 C54 1.344(6) . ? C43 C68 1.413(7) . ? C44 C61 1.423(7) . ? C45 C71 1.352(6) . ? C46 C65 1.370(6) . ? C47 C73 1.424(6) . ? C47 C55 1.427(6) . ? C48 C60 1.371(6) . ? C48 C53 1.372(6) . ? C49 C62 1.365(7) . ? C49 C66 1.416(7) . ? C50 C73 1.382(6) . ? C52 C64 1.418(7) 2_665 ? C53 C58 1.375(6) . ? C54 C56 1.427(6) . ? C55 C70 1.345(6) . ? C56 C72 1.433(6) . ? C58 C69 1.391(5) . ? C59 C73 1.431(6) . ? C60 C63 1.383(5) . ? C63 C69 1.392(5) . ? C64 C52 1.418(7) 2_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 C95 C20 116.2(13) . . ? C19 N4 C20 120.1(11) . . ? C56 C94 C23 120.6(4) . . ? C51 N3 C72 118.6(3) . . ? C27 N2 C32 117.5(4) . . ? C57 N1 C47 118.1(4) . . ? C52 C18 C19 121.2(4) . . ? N4 C19 C20 122.0(8) . 2_665 ? N4 C19 C18 119.9(8) . . ? C20 C19 C18 118.1(4) 2_665 . ? N4 C19 C95 2.7(13) . . ? C20 C19 C95 119.6(8) 2_665 . ? C18 C19 C95 122.3(8) . . ? N4 C20 C19 118.0(6) . 2_665 ? N4 C20 C31 123.0(7) . . ? C19 C20 C31 119.0(4) 2_665 . ? N4 C20 C95 6.4(12) . . ? C19 C20 C95 124.2(8) 2_665 . ? C31 C20 C95 116.7(8) . . ? C26 C21 C34 120.3(4) . . ? C35 C22 C38 120.9(5) . . ? C94 C23 C45 123.3(4) . . ? C94 C23 C51 117.3(4) . . ? C45 C23 C51 119.4(4) . . ? C68 C24 C72 120.3(4) . . ? C59 C25 C70 120.7(5) . . ? C21 C26 C41 122.8(4) . . ? C21 C26 C32 118.2(4) . . ? C41 C26 C32 119.0(4) . . ? N2 C27 C37 118.9(4) . . ? N2 C27 C34 123.6(4) . . ? C37 C27 C34 117.5(4) . . ? C44 C28 C32 120.7(4) . . ? C40 C29 C71 121.5(4) . . ? F6 C30 C67 120.8(4) . . ? F6 C30 C36 117.0(4) . . ? C67 C30 C36 122.2(4) . . ? C64 C31 C20 120.4(4) . . ? N2 C32 C28 118.6(4) . . ? N2 C32 C26 123.0(4) . . ? C28 C32 C26 118.4(4) . . ? C38 C33 C39 120.3(5) . . ? C21 C34 C62 123.7(4) . . ? C21 C34 C27 117.1(4) . . ? C62 C34 C27 119.2(4) . . ? C22 C35 C57 121.1(5) . . ? F12 C36 C65 120.3(4) . . ? F12 C36 C30 121.1(4) . . ? C65 C36 C30 118.6(4) . . ? C66 C37 C27 121.2(4) . . ? C33 C38 C22 120.5(4) . . ? C50 C39 C57 117.2(4) . . ? C50 C39 C33 123.3(4) . . ? C57 C39 C33 119.5(4) . . ? C29 C40 C51 120.2(4) . . ? C61 C41 C26 121.0(4) . . ? C46 C42 C67 118.4(4) . . ? C46 C42 I1 118.0(3) . . ? C67 C42 I1 123.6(3) . . ? C54 C43 C68 120.5(4) . . ? C28 C44 C61 120.4(4) . . ? C71 C45 C23 120.5(4) . . ? F10 C46 C65 117.5(4) . . ? F10 C46 C42 120.6(4) . . ? C65 C46 C42 121.9(4) . . ? N1 C47 C73 122.6(4) . . ? N1 C47 C55 118.9(4) . . ? C73 C47 C55 118.4(4) . . ? F9 C48 C60 120.5(4) . . ? F9 C48 C53 119.5(4) . . ? C60 C48 C53 120.0(4) . . ? C62 C49 C66 119.4(4) . . ? C73 C50 C39 120.6(4) . . ? N3 C51 C40 119.0(4) . . ? N3 C51 C23 122.9(4) . . ? C40 C51 C23 118.1(4) . . ? C18 C52 C64 120.7(4) . 2_665 ? F8 C53 C48 120.2(4) . . ? F8 C53 C58 121.0(4) . . ? C48 C53 C58 118.9(4) . . ? C43 C54 C56 120.9(4) . . ? C70 C55 C47 120.6(5) . . ? C94 C56 C54 123.1(4) . . ? C94 C56 C72 118.3(4) . . ? C54 C56 C72 118.6(4) . . ? N1 C57 C39 123.2(4) . . ? N1 C57 C35 119.1(4) . . ? C39 C57 C35 117.7(4) . . ? F7 C58 C53 117.4(4) . . ? F7 C58 C69 120.3(4) . . ? C53 C58 C69 122.3(4) . . ? C25 C59 C73 119.7(5) . . ? F11 C60 C48 117.7(4) . . ? F11 C60 C63 120.8(4) . . ? C48 C60 C63 121.5(4) . . ? C41 C61 C44 120.3(4) . . ? C49 C62 C34 121.3(4) . . ? C60 C63 C69 119.3(4) . . ? C60 C63 I3 117.0(3) . . ? C69 C63 I3 123.6(3) . . ? C31 C64 C52 120.5(4) . 2_665 ? F5 C65 C46 120.4(4) . . ? F5 C65 C36 119.5(4) . . ? C46 C65 C36 120.1(4) . . ? C37 C66 C49 121.3(4) . . ? C30 C67 C42 118.7(4) . . ? C30 C67 I2 117.9(3) . . ? C42 C67 I2 123.4(3) . . ? C24 C68 C43 121.0(4) . . ? C58 C69 C63 118.0(4) . . ? C58 C69 I4 117.1(3) . . ? C63 C69 I4 124.8(3) . . ? C55 C70 C25 121.1(5) . . ? C45 C71 C29 120.3(4) . . ? N3 C72 C24 119.2(4) . . ? N3 C72 C56 122.2(4) . . ? C24 C72 C56 118.6(4) . . ? C50 C73 C47 118.2(4) . . ? C50 C73 C59 122.3(4) . . ? C47 C73 C59 119.5(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.786 _refine_diff_density_min -0.982 _refine_diff_density_rms 0.156 data_(1,2-tfib)-(phen) _database_code_depnum_ccdc_archive 'CCDC 795736' #TrackingRef '- deposit_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; phenazine:tetrafluoro-1,2-diiodobenzene 1/1 ; _chemical_name_common 'phenazine:tetrafluoro-1,2-diiodobenzene 1/1' _chemical_melting_point ? _chemical_formula_moiety '(C12 H8 N2) (C6 F4 I2)' _chemical_formula_sum 'C18 H8 F4 I2 N2' _chemical_formula_weight 582.1 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3077(3) _cell_length_b 7.6892(2) _cell_length_c 20.0916(4) _cell_angle_alpha 90.00 _cell_angle_beta 125.881(1) _cell_angle_gamma 90.00 _cell_volume 1790.92(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9522 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 3.555 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.662 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15365 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.97 _reflns_number_total 5665 _reflns_number_gt 3859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The asymmetric unit has one tppo molecule in a general position and two half 1,4-tfib molecules each lying about independent inversion centres. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+1.2134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5665 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4872(4) 0.1037(6) 0.0481(3) 0.0318(9) Uani 1 1 d . . . C2 C 0.4782(4) 0.2197(7) 0.0996(3) 0.0383(11) Uani 1 1 d . . . H2 H 0.4311 0.1912 0.1158 0.046 Uiso 1 1 calc R . . C3 C 0.5384(4) 0.3723(7) 0.1251(3) 0.0404(11) Uani 1 1 d . . . H3 H 0.5328 0.4461 0.1593 0.048 Uiso 1 1 calc R . . C4 C 0.6090(4) 0.4193(7) 0.1003(3) 0.0414(11) Uani 1 1 d . . . H4 H 0.6485 0.5246 0.1175 0.050 Uiso 1 1 calc R . . C5 C 0.6199(4) 0.3115(7) 0.0511(3) 0.0404(11) Uani 1 1 d . . . H5 H 0.6672 0.3436 0.0355 0.049 Uiso 1 1 calc R . . C6 C 0.0747(4) 0.1085(6) 0.4999(3) 0.0327(9) Uani 1 1 d . . . C7 C 0.5596(4) 0.1514(6) 0.0236(3) 0.0320(9) Uani 1 1 d . . . C8 C 0.0255(4) -0.0388(6) 0.4467(3) 0.0339(10) Uani 1 1 d . . . C9 C 0.0552(4) -0.0714(7) 0.3913(3) 0.0390(10) Uani 1 1 d . . . H9 H 0.0254 -0.1683 0.3571 0.047 Uiso 1 1 calc R . . C10 C 0.1271(5) 0.0393(7) 0.3883(3) 0.0432(12) Uani 1 1 d . . . H10 H 0.1438 0.0195 0.3506 0.052 Uiso 1 1 calc R . . C11 C 0.1767(5) 0.1839(7) 0.4417(3) 0.0440(12) Uani 1 1 d . . . H11 H 0.2269 0.2566 0.4397 0.053 Uiso 1 1 calc R . . C12 C 0.1517(5) 0.2173(7) 0.4959(3) 0.0450(12) Uani 1 1 d . . . H12 H 0.1853 0.3124 0.5310 0.054 Uiso 1 1 calc R . . C13 C 0.2697(4) 0.6774(6) 0.1765(3) 0.0373(10) Uani 1 1 d . . . C14 C 0.3159(5) 0.5164(7) 0.2130(3) 0.0491(14) Uani 1 1 d . . . C15 C 0.2897(6) 0.4411(8) 0.2623(3) 0.0588(17) Uani 1 1 d . . . C16 C 0.2176(6) 0.5208(9) 0.2753(3) 0.0601(19) Uani 1 1 d . . . C17 C 0.1695(5) 0.6809(8) 0.2392(3) 0.0499(14) Uani 1 1 d . . . C18 C 0.1946(5) 0.7623(7) 0.1893(3) 0.0386(11) Uani 1 1 d . . . F1 F 0.3871(3) 0.4302(5) 0.2024(2) 0.0672(10) Uani 1 1 d . . . F2 F 0.3384(4) 0.2895(5) 0.3002(2) 0.0872(14) Uani 1 1 d . . . F3 F 0.1906(4) 0.4492(6) 0.3228(2) 0.0936(16) Uani 1 1 d . . . F4 F 0.0973(4) 0.7592(6) 0.2523(2) 0.0729(12) Uani 1 1 d . . . I1 I 0.32458(3) 0.78597(5) 0.109664(19) 0.03977(11) Uani 1 1 d . . . I2 I 0.12388(3) 1.00652(4) 0.13886(2) 0.04275(11) Uani 1 1 d . . . N1 N 0.4285(3) -0.0469(5) 0.0247(2) 0.0340(8) Uani 1 1 d . . . N2 N -0.0483(3) -0.1471(6) 0.4471(2) 0.0369(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(2) 0.036(3) 0.025(2) -0.0002(18) 0.0118(17) 0.0040(18) C2 0.037(2) 0.044(3) 0.039(3) -0.002(2) 0.026(2) 0.003(2) C3 0.038(2) 0.041(3) 0.036(2) -0.004(2) 0.018(2) 0.008(2) C4 0.040(2) 0.040(3) 0.038(3) -0.007(2) 0.020(2) -0.001(2) C5 0.036(2) 0.043(3) 0.042(3) -0.004(2) 0.023(2) -0.003(2) C6 0.032(2) 0.035(3) 0.031(2) 0.0054(19) 0.0179(19) 0.0055(19) C7 0.027(2) 0.038(3) 0.029(2) 0.0026(19) 0.0151(18) 0.0045(18) C8 0.032(2) 0.037(3) 0.028(2) 0.0072(18) 0.0155(19) 0.0056(19) C9 0.039(2) 0.041(3) 0.038(2) 0.000(2) 0.024(2) 0.004(2) C10 0.041(3) 0.058(3) 0.038(3) 0.009(2) 0.028(2) 0.007(2) C11 0.044(3) 0.052(3) 0.044(3) 0.009(2) 0.030(2) -0.002(2) C12 0.042(3) 0.046(3) 0.047(3) -0.003(2) 0.026(2) -0.009(2) C13 0.040(2) 0.037(3) 0.029(2) 0.0002(19) 0.016(2) -0.007(2) C14 0.055(3) 0.039(3) 0.036(3) -0.002(2) 0.017(3) -0.010(2) C15 0.067(4) 0.045(3) 0.034(3) 0.006(2) 0.014(3) -0.021(3) C16 0.081(4) 0.063(4) 0.029(3) -0.006(2) 0.028(3) -0.043(4) C17 0.062(3) 0.060(4) 0.037(3) -0.017(2) 0.034(3) -0.027(3) C18 0.047(3) 0.037(3) 0.029(2) -0.0030(19) 0.020(2) -0.012(2) F1 0.064(2) 0.046(2) 0.070(2) 0.0075(19) 0.027(2) 0.0143(18) F2 0.102(3) 0.049(2) 0.057(2) 0.0231(18) 0.016(2) -0.019(2) F3 0.128(4) 0.101(3) 0.053(2) 0.001(2) 0.054(3) -0.059(3) F4 0.089(3) 0.094(3) 0.067(2) -0.027(2) 0.063(2) -0.037(2) I1 0.04133(18) 0.0421(2) 0.03879(18) -0.00094(14) 0.02512(15) -0.00120(14) I2 0.04279(19) 0.0405(2) 0.0453(2) -0.00802(15) 0.02601(16) -0.00359(14) N1 0.0343(19) 0.036(2) 0.033(2) -0.0017(17) 0.0206(17) 0.0009(17) N2 0.036(2) 0.034(2) 0.038(2) -0.0002(18) 0.0201(18) -0.0014(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(6) . ? C1 C2 1.429(6) . ? C1 C7 1.430(6) . ? C2 C3 1.365(7) . ? C2 H2 0.9300 . ? C3 C4 1.412(7) . ? C3 H3 0.9300 . ? C4 C5 1.367(7) . ? C4 H4 0.9300 . ? C5 C7 1.417(7) . ? C5 H5 0.9300 . ? C6 N2 1.355(6) 3_556 ? C6 C12 1.422(7) . ? C6 C8 1.428(7) . ? C7 N1 1.346(6) 3_655 ? C8 N2 1.348(6) . ? C8 C9 1.428(6) . ? C9 C10 1.364(7) . ? C9 H9 0.9300 . ? C10 C11 1.414(8) . ? C10 H10 0.9300 . ? C11 C12 1.356(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.392(7) . ? C13 C18 1.405(7) . ? C13 I1 2.086(5) . ? C14 F1 1.334(7) . ? C14 C15 1.375(8) . ? C15 F2 1.342(7) . ? C15 C16 1.351(10) . ? C16 F3 1.340(6) . ? C16 C17 1.389(9) . ? C17 F4 1.349(7) . ? C17 C18 1.395(7) . ? C18 I2 2.091(5) . ? N1 C7 1.346(6) 3_655 ? N2 C6 1.355(6) 3_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 119.2(4) . . ? N1 C1 C7 122.1(4) . . ? C2 C1 C7 118.7(4) . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 120.6(5) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C7 120.4(5) . . ? C4 C5 H5 119.8 . . ? C7 C5 H5 119.8 . . ? N2 C6 C12 119.8(5) 3_556 . ? N2 C6 C8 121.3(4) 3_556 . ? C12 C6 C8 118.9(4) . . ? N1 C7 C5 119.6(4) 3_655 . ? N1 C7 C1 121.2(4) 3_655 . ? C5 C7 C1 119.2(4) . . ? N2 C8 C6 122.0(4) . . ? N2 C8 C9 119.2(5) . . ? C6 C8 C9 118.8(4) . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.8(5) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.5(5) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C6 120.8(5) . . ? C11 C12 H12 119.6 . . ? C6 C12 H12 119.6 . . ? C14 C13 C18 119.6(5) . . ? C14 C13 I1 117.0(4) . . ? C18 C13 I1 123.3(4) . . ? F1 C14 C15 117.5(6) . . ? F1 C14 C13 121.9(5) . . ? C15 C14 C13 120.6(6) . . ? F2 C15 C16 119.0(6) . . ? F2 C15 C14 120.3(7) . . ? C16 C15 C14 120.6(6) . . ? F3 C16 C15 121.6(7) . . ? F3 C16 C17 118.3(7) . . ? C15 C16 C17 120.1(5) . . ? F4 C17 C16 119.7(5) . . ? F4 C17 C18 119.2(6) . . ? C16 C17 C18 121.1(6) . . ? C17 C18 C13 118.0(5) . . ? C17 C18 I2 119.8(4) . . ? C13 C18 I2 122.2(3) . . ? C1 N1 C7 116.6(4) . 3_655 ? C8 N2 C6 116.7(4) . 3_556 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.779 _refine_diff_density_min -1.538 _refine_diff_density_rms 0.269 data_(1,4-tfib)-(tppo) _database_code_depnum_ccdc_archive 'CCDC 795737' #TrackingRef '- deposit_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triphenylphosphine oxide:1,4-diiodotetrafluorobenzene 1:1 ; _chemical_name_common 'triphenylphosphine oxide:1,4-diiodotetrafluorobenzene 1:1' _chemical_melting_point ? _chemical_formula_moiety '(C18 H16 P O) (C6 F4 I2)' _chemical_formula_sum 'C24 H15 F4 I2 O P' _chemical_formula_weight 680.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8642(2) _cell_length_b 8.3329(1) _cell_length_c 18.4437(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.542(1) _cell_angle_gamma 90.00 _cell_volume 2337.25(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16253 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 2.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.686 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 28983 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6815 _reflns_number_gt 4808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All atoms were refined using the anisotropic model. Hydrogen atoms bonded of hydrocarbon groups were placed in positions calculated on the basis of the hybridisation of the belonging carbon atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+1.8004P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6815 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0451(2) 0.3182(4) 0.65915(16) 0.0288(6) Uani 1 1 d . . . C2 C 0.0245(2) 0.2206(4) 0.71321(19) 0.0393(8) Uani 1 1 d . . . H2 H 0.0670 0.1472 0.7417 0.047 Uiso 1 1 calc R . . C3 C -0.0575(3) 0.2303(5) 0.7255(2) 0.0463(9) Uani 1 1 d . . . H3 H -0.0708 0.1640 0.7627 0.056 Uiso 1 1 calc R . . C4 C -0.1196(3) 0.3353(4) 0.6843(2) 0.0452(9) Uani 1 1 d . . . H4 H -0.1762 0.3401 0.6923 0.054 Uiso 1 1 calc R . . C5 C -0.0997(2) 0.4338(4) 0.6313(2) 0.0397(8) Uani 1 1 d . . . H5 H -0.1426 0.5066 0.6029 0.048 Uiso 1 1 calc R . . C6 C -0.0176(2) 0.4271(4) 0.61932(18) 0.0347(7) Uani 1 1 d . . . H6 H -0.0039 0.4972 0.5837 0.042 Uiso 1 1 calc R . . C7 C 0.1378(2) 0.2244(3) 0.55091(17) 0.0312(7) Uani 1 1 d . . . C8 C 0.0562(2) 0.1867(4) 0.50137(18) 0.0369(7) Uani 1 1 d . . . H8 H 0.0044 0.2005 0.5168 0.044 Uiso 1 1 calc R . . C9 C 0.0501(3) 0.1288(4) 0.4294(2) 0.0469(9) Uani 1 1 d . . . H9 H -0.0058 0.1042 0.3955 0.056 Uiso 1 1 calc R . . C10 C 0.1253(3) 0.1069(4) 0.4070(2) 0.0495(10) Uani 1 1 d . . . H10 H 0.1211 0.0675 0.3578 0.059 Uiso 1 1 calc R . . C11 C 0.2065(3) 0.1421(4) 0.4560(2) 0.0505(10) Uani 1 1 d . . . H11 H 0.2582 0.1258 0.4407 0.061 Uiso 1 1 calc R . . C12 C 0.2131(2) 0.2008(4) 0.5273(2) 0.0410(8) Uani 1 1 d . . . H12 H 0.2693 0.2254 0.5606 0.049 Uiso 1 1 calc R . . C13 C 0.1928(2) 0.5037(4) 0.64378(17) 0.0288(6) Uani 1 1 d . . . C14 C 0.1651(2) 0.6009(4) 0.58073(19) 0.0365(8) Uani 1 1 d . . . H14 H 0.1278 0.5582 0.5351 0.044 Uiso 1 1 calc R . . C15 C 0.1914(2) 0.7606(4) 0.5835(2) 0.0391(8) Uani 1 1 d . . . H15 H 0.1716 0.8275 0.5403 0.047 Uiso 1 1 calc R . . C16 C 0.2468(2) 0.8203(4) 0.6499(2) 0.0374(8) Uani 1 1 d . . . H16 H 0.2639 0.9299 0.6527 0.045 Uiso 1 1 calc R . . C17 C 0.2772(2) 0.7230(4) 0.71207(19) 0.0383(8) Uani 1 1 d . . . H17 H 0.3172 0.7643 0.7568 0.046 Uiso 1 1 calc R . . C18 C 0.2498(2) 0.5645(4) 0.70961(18) 0.0342(7) Uani 1 1 d . . . H18 H 0.2700 0.4978 0.7529 0.041 Uiso 1 1 calc R . . C19 C 0.4376(2) 0.4478(4) 0.43340(17) 0.0323(7) Uani 1 1 d . . . C20 C 0.4135(2) 0.4922(4) 0.49669(18) 0.0364(7) Uani 1 1 d . . . C21 C 0.4739(2) 0.5434(4) 0.56175(18) 0.0358(7) Uani 1 1 d . . . C22 C 0.5094(2) 0.5311(4) 0.92765(18) 0.0390(8) Uani 1 1 d . . . C23 C 0.4374(2) 0.5860(4) 0.94796(19) 0.0385(8) Uani 1 1 d . . . C24 C 0.5716(2) 0.4444(4) 0.9810(2) 0.0393(8) Uani 1 1 d . . . F1 F 0.32807(13) 0.4874(3) 0.49522(12) 0.0571(6) Uani 1 1 d . . . F2 F 0.44564(14) 0.5842(3) 0.62137(11) 0.0527(6) Uani 1 1 d . . . F3 F 0.37421(15) 0.6690(3) 0.89894(12) 0.0547(6) Uani 1 1 d . . . F4 F 0.64282(14) 0.3856(3) 0.96471(12) 0.0551(6) Uani 1 1 d . . . I1 I 0.344381(14) 0.37270(3) 0.334170(11) 0.03362(7) Uani 1 1 d . . . I2 I 0.525207(19) 0.57770(4) 0.821753(15) 0.05971(10) Uani 1 1 d . . . O1 O 0.21293(15) 0.2005(3) 0.70491(13) 0.0390(5) Uani 1 1 d . . . P1 P 0.15298(5) 0.30087(9) 0.64533(4) 0.02893(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0357(16) 0.0239(14) 0.0231(14) -0.0019(12) 0.0024(12) -0.0057(13) C2 0.053(2) 0.0301(18) 0.0318(17) 0.0057(14) 0.0074(16) -0.0014(16) C3 0.058(2) 0.048(2) 0.0377(19) 0.0044(16) 0.0202(18) -0.0077(18) C4 0.046(2) 0.050(2) 0.045(2) -0.0051(17) 0.0201(18) -0.0049(17) C5 0.0412(19) 0.0399(19) 0.0390(19) -0.0001(15) 0.0130(16) 0.0015(16) C6 0.0413(19) 0.0310(17) 0.0294(17) 0.0029(13) 0.0062(14) 0.0012(14) C7 0.0431(18) 0.0210(15) 0.0265(15) 0.0040(12) 0.0049(14) 0.0000(13) C8 0.0439(19) 0.0350(17) 0.0290(16) -0.0044(14) 0.0058(15) -0.0024(15) C9 0.062(2) 0.040(2) 0.0314(18) -0.0055(15) 0.0019(17) -0.0084(18) C10 0.084(3) 0.036(2) 0.0310(18) -0.0017(15) 0.021(2) 0.000(2) C11 0.067(3) 0.044(2) 0.047(2) 0.0050(18) 0.027(2) 0.006(2) C12 0.0415(19) 0.042(2) 0.0383(19) 0.0034(16) 0.0090(16) 0.0034(16) C13 0.0295(15) 0.0281(16) 0.0256(15) 0.0005(12) 0.0028(12) 0.0010(13) C14 0.0366(17) 0.0372(19) 0.0305(17) 0.0038(14) 0.0012(14) -0.0048(14) C15 0.0390(18) 0.0369(19) 0.0399(19) 0.0130(15) 0.0091(16) -0.0036(15) C16 0.0355(18) 0.0294(16) 0.049(2) -0.0026(15) 0.0153(16) -0.0047(14) C17 0.0398(19) 0.0345(18) 0.0365(18) -0.0078(15) 0.0043(15) -0.0053(15) C18 0.0378(18) 0.0306(16) 0.0290(16) 0.0015(13) 0.0011(14) -0.0003(14) C19 0.0364(17) 0.0341(17) 0.0214(15) -0.0021(13) 0.0002(13) -0.0023(14) C20 0.0286(16) 0.048(2) 0.0289(16) -0.0041(15) 0.0025(13) -0.0078(15) C21 0.0374(18) 0.0426(19) 0.0267(16) -0.0051(14) 0.0083(14) -0.0017(15) C22 0.0433(19) 0.047(2) 0.0279(17) -0.0008(15) 0.0119(15) -0.0067(16) C23 0.0368(18) 0.044(2) 0.0322(17) 0.0016(15) 0.0056(15) 0.0012(15) C24 0.0364(18) 0.047(2) 0.0369(19) -0.0026(16) 0.0149(16) -0.0001(16) F1 0.0326(11) 0.0946(18) 0.0438(12) -0.0205(12) 0.0105(10) -0.0109(11) F2 0.0458(12) 0.0852(16) 0.0288(11) -0.0177(10) 0.0135(10) -0.0073(11) F3 0.0502(13) 0.0726(15) 0.0399(12) 0.0109(11) 0.0106(10) 0.0154(11) F4 0.0439(12) 0.0821(17) 0.0450(13) 0.0009(11) 0.0217(11) 0.0131(11) I1 0.03617(11) 0.03573(12) 0.02382(10) -0.00223(8) 0.00025(8) -0.00433(9) I2 0.05806(17) 0.0914(2) 0.03424(14) 0.01265(13) 0.02047(13) 0.00703(15) O1 0.0425(13) 0.0315(12) 0.0333(12) 0.0059(10) -0.0051(10) 0.0066(10) P1 0.0324(4) 0.0252(4) 0.0235(4) 0.0030(3) -0.0014(3) 0.0014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.392(4) . ? C1 C2 1.395(4) . ? C1 P1 1.807(3) . ? C2 C3 1.385(5) . ? C2 H2 0.9500 . ? C3 C4 1.375(5) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 H4 0.9500 . ? C5 C6 1.381(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.392(4) . ? C7 C12 1.397(5) . ? C7 P1 1.805(3) . ? C8 C9 1.390(5) . ? C8 H8 0.9500 . ? C9 C10 1.381(6) . ? C9 H9 0.9500 . ? C10 C11 1.378(6) . ? C10 H10 0.9500 . ? C11 C12 1.378(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 C18 1.387(4) . ? C13 P1 1.808(3) . ? C14 C15 1.391(5) . ? C14 H14 0.9500 . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 C17 1.375(5) . ? C16 H16 0.9500 . ? C17 C18 1.387(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.379(4) . ? C19 C21 1.382(5) 3_666 ? C19 I1 2.095(3) . ? C20 F1 1.348(4) . ? C20 C21 1.374(4) . ? C21 F2 1.345(4) . ? C21 C19 1.382(5) 3_666 ? C22 C23 1.379(5) . ? C22 C24 1.381(5) . ? C22 I2 2.075(3) . ? C23 F3 1.336(4) . ? C23 C24 1.381(5) 3_667 ? C24 F4 1.342(4) . ? C24 C23 1.381(5) 3_667 ? O1 P1 1.489(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.7(3) . . ? C6 C1 P1 122.7(2) . . ? C2 C1 P1 118.5(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C8 C7 C12 118.8(3) . . ? C8 C7 P1 123.8(3) . . ? C12 C7 P1 117.4(3) . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C7 120.5(3) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C18 119.7(3) . . ? C14 C13 P1 122.2(2) . . ? C18 C13 P1 118.1(2) . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.0(3) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 119.8(3) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C21 116.9(3) . 3_666 ? C20 C19 I1 121.5(2) . . ? C21 C19 I1 121.6(2) 3_666 . ? F1 C20 C21 118.3(3) . . ? F1 C20 C19 119.7(3) . . ? C21 C20 C19 122.0(3) . . ? F2 C21 C20 118.7(3) . . ? F2 C21 C19 120.2(3) . 3_666 ? C20 C21 C19 121.1(3) . 3_666 ? C23 C22 C24 117.3(3) . . ? C23 C22 I2 121.7(3) . . ? C24 C22 I2 121.0(3) . . ? F3 C23 C22 120.5(3) . . ? F3 C23 C24 118.5(3) . 3_667 ? C22 C23 C24 120.9(3) . 3_667 ? F4 C24 C22 120.5(3) . . ? F4 C24 C23 117.7(3) . 3_667 ? C22 C24 C23 121.8(3) . 3_667 ? O1 P1 C7 113.30(14) . . ? O1 P1 C1 111.87(14) . . ? C7 P1 C1 107.02(15) . . ? O1 P1 C13 112.58(14) . . ? C7 P1 C13 105.43(14) . . ? C1 P1 C13 106.11(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.633 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.112